The Pathless Path with Paul Millerd

Alex was crushing it early in his career, ending up on Wall Street after getting a combined JD/MBA.  But after a few years, he went looking for his next mountain, aiming his ambition at the tech sector. He ended up co-founding LiveOak, a company he eventually sold in 2020. After that, he struggled to determine what was next and finally decided to walk away from more than a million dollars. Now he's embracing non-doing, reconnecting with his passions, and figuring out what's next. 🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @CantHardyWait⌛TIMESTAMPS(01:08) - The scripts Alex grew up with (10:06) - Law School & Business School (22:41) - Wall Street, Banking & The Pride in suffering (30:55) - Tech Start-ups, coffee meetings and friendlessness (56:19) - Exiting his tech company & "Total Work" (01:14:24) - His Sabbatical, Finding Work Worth Doing & The American Mind (01:21:05) - Forgotten Hobbies, Borders & The Love for The Present (01:29:02) - Closing remarks 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

In 2015 Khe left a Wall Street carrier to pursue his own path of "uncomfortable introspection", reevaluating his life. This is a constant process - Khe is always being emergent to himself. Now he finds himself at a crossroads - after a great initial success in 2020, he recently had to scale down his cohort-based course. Although laying people off was tough, Khe welcomes the change as entering a new season of creativity.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @khemaridhradreads.coDownload Khe's Free Money Guide⌛TIMESTAMPS(01:43) - Leaving Wallstreet behind (08:16) - Money, Winning and Fears (13:04) - Sharing online, spending money and investing (18:16) - Coaching and marriage (22:27) - Leading online courses (33:14) - Organizational complexity vs $10 work (39:57) - Shutting down his course (52:39) - Cohorts vs self-based courses (54:15) - Writing and selling books (01:02:32) - Creativity vs productivity (01:07:36) - Closing remarks 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Kyle was a marketing executive who believed in the "hard work" ethic. After an existential crisis, he decided to carve his own path as a solopreneur and started Sloww - "a trusted resource of lifelong learning". Kyle describes his purpose as "synthesizing the art of living for students of life".🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @KyKowSloww: sloww.coHappiness BookIgikai 2.0⌛TIMESTAMPS(01:22) - The scripts that Kyle grew up with (13:59) - How to have an existential crisis (30:29) - Decompressing from his career (43:17) - Sloww, thinking and the art of living (53:37) - Kyle's next phase, sharing the personal story (01:03:19) - Long form content, Kyle's course on synthesis (01:09:33) - Where can we find Kyle? (01:10:04) - Thanks and Goodbyes 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Kevin is the founding executive editor of Wired magazine, a writer and a photographer. When he was young he dropped out of college and travelled to Taiwan, which he describes as a live changing experience. Kevin is passionate about owning his time, the importance of goofing off and staying optimistic about the development of technology.🎥🍿 YOUTUBE: WATCH HERELinks:Kevin's website: kk.orgKevin's articles on WiredExcellent Advice on Living: Amazon⌛TIMESTAMPS(01:01) - Taiwan and the importance of travel (09:31) - Owning time instead of money (14:50) - Work, rest ethic, taking time to goof off (25:35) - Riding his bike across US (29:23) - YouTube (33:50) - Patience, optimism and technological changes (40:37) - Raising Children (45:48) - Kevin's book and the power of outsourcing 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Billy used to be an avid skier, working odd jobs and traveling between the northern and southern hemispheres trying to catch the best skiing. In 2018 he e-mailed Ryan Holiday and pitched him on doing some work for him for free. In a couple of months, he was hired as Ryan's research assistant.  Billy is one of the most curious people I know and we dive into his journey. 🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @bpoppenheimerWebsite: billyoppenheimer.comBilly's Newsletter⌛TIMESTAMPS(00:56) - The scripts Billy grew up with (13:45) - Reaching out to Ryan Holiday (17:52) - The research process and learning from Ryan (25:21) - Skiing, Australia and finding his own voice (40:23) - Animal courtship (43:42) - How Ryan Holiday manages his team (51:42) - Ambition and learning from past models (01:03:10) - Downsides to fame (01:04:01) - Where can we find Biilly? 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

I'm sharing this conversation I had a couple of months ago with Tom Peters. Our convo got cut a bit short but it was a fun conversation reflecting on his trajectory, why he got kicked out of McKinseyTo learn more about Tom: His Website 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Trung is a writer at Workweek, cofounder of bearly.ai, and co-host of the Not Investment Advice podcast. He is passionate about playing the long game and unleashing the power of compounding.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @TrungTPhanWebsite: trungtphan.comBearly.AIPodcast: Not Investment AdviceTrung's writing at Bloomberg and Workweek Trung's Newsletter⌛TIMESTAMPS(02:12) - College and getting up late (04:44) - Trung's great grandfather - Vietnamese hero (09:31) - Vietnam, important lessons from living abroad (22:05) - Writing & productivity (42:49) - Kids, work & flexibility (46:43) - Playing the long game 📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Steph Smith is the host of the  a16z podcast and is an online creator, former consultant, former digital nomad and all-around badass.  We talk about money, work, relationships, and weddings...🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @stephsmithioSteph's book: doingcontentright.coma16z PodcastThe Sh*t You Don't Learn in School PodcastBlog: stephsmith.io⌛TIMESTAMPS(01:19) - The scripts that Steph grew up with (03:47) - Perceptions of money over time (29:15) - Working at The Hustle (33:57) - A16Z and Beginner's Mindset (38:04) - Solving the life puzzle with a partner (46:56) - Scripts around kids (52:20) - Avoiding long wedding planning cycles (56:10) - Full-time employment and podcasting (58:01) - Opportunities in the creator economy (01:02:23) - Is Paul underpricing his book? (01:05:57) - The most interesting opportunities in the creator economy   📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Russ is an economist, a research fellow at Stanford University's Hoover Institution and president of Shalem College in Jerusalem. One of pioneers of podcasting, he's been hosting EconTalk since 2006.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @EconTalkerEconTalk Website: www.econtalk.orgEconTalk YouTube Channel⌛TIMESTAMPS(03:25) - The influence of Russ' father (11:13) - What modern economics often fails to observe (16:15) - Adam Smith and human nature (27:05) - Starting EconTalk in 2006 (40:42) - Moving to Israel in his 60's (45:35) - How people misunderstand the Academia (49:43) - How Russ' approach to his podcast developed over time (53:01) - The metaphor of a conversation (57:11) - Mortality & fatherhood (01:03:49) - Russ' dream guest and what's next 📕Buy Paul’s Book: The Pathless Path🤝Join Find The Others: A Community For People On Unconventional Paths📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here

Sam is a partner at The Ready - an organizational design consultancy operating fully remotely. He is also a prolific writer, passionate about personal development, self-managing organizations and adopting a more human, adaptive, and meaningful way of working.🎥🍿 YOUTUBE: WATCH HERELinks:Twitter: @samspurlinInstagram: samspurlinLinkedIn: linkedin.com/in/samspurlinSam's writing: samspurlin.com/writingSam's writing on Medium: samspurlin.medium.comNewsletter: thedeliberate.substack.com/p/landing-page⌛TIMESTAMPS(00:53) - The scripts that Sam grew up with (10:09) - Teaching and why Sam quit (17:10) - Claremont and letting go of the PhD (25:49) - Working pro bono to become a consultant (31:26) - Complicated vs complex systems, ego in the organizations (53:49) - Writing, podcasting, farming and retrospective meetings (01:02:02) - The trap of a "dream job" (01:05:27) - Closing remarks 📕Buy Paul’s Book (Published Jan 2022): The Pathless Path😁👉😁 Want To Connect, Create & Root For Others On The Pathless Path? - Join 100+ Others In The Find The Others Community📲Connect + Follow PaulTwitter: @p_millerdPaul’s Newsletter: Subscribe to BoundlessPaul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:I use Transistor to host this podcast. It rocks. Launch Your HereI record high-quality video using Riverside: Sign Up HereBecome a sponsor of the Podcast / NewsletterWant to upgrade your Zoom studio? Check out Kevin Shen’s Dream Studio CourseWant to launch a course? Podia or Teachable are both greatWeb Hosting: Skystra Fast WordPress HostingHost your own community" Circle 14-day free trial 📘 GOOD WORK: LIVE! => Learn More📕 Buy Paul’s Book (50k+ Sold): The Pathless Path😁 Join Hundreds On Unconventional Paths: Pathless Path Community📲Connect + Follow PaulTwitter: @p_millerdInstagram: @pathlesspaulPaul’s Newsletter: Subscribe to Pathless (23k+ People)Paul’s YouTube: Subscribe🙏Further Ways To Support The Podcast:Accounting, Taxes, And Payroll For Your S-Corp (Ideal for $60k+ income): CollectiveLooking for alternatives to traditional health insurance in the US? Check out CrowdhealthI use Transistor to host this podcast. It rocks. Launch Yours HereI record high-quality videos using Riverside: Sign Up Here